Water → 2-[2-Amino-4-(1,3-dihydroisoindole-2-carbonyl)quinazolin-6-yl]-4,5-difluorobenzyl propionate

HRID 1631166Notes

Reaction equation

[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[NH2:6][C:7]1[N:16]=[C:15]([C:17]([N:19]2[CH2:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20]2)=[O:18])[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:28]3[CH:33]=[C:32]([F:34])[C:31]([F:35])=[CH:30][C:29]=3[CH2:36][OH:37])[CH:13]=2)[N:8]=1.C(OCC)(=O)C.O>CN(C)C1C=CN=CC=1.CN(C)C=O>[C:1]([O:37][CH2:36][C:29]1[CH:30]=[C:31]([F:35])[C:32]([F:34])=[CH:33][C:28]=1[C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH2:6])[N:16]=[C:15]2[C:17]([N:19]1[CH2:20][C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:27]1)=[O:18])(=[O:4])[CH2:2][CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

33 μl of propionyl chloride are added to a solution of 150 mg of [2-amino-6-(4,5-difluoro-2-hydroxymethylphenyl)quinazolin-4-yl]-(1,3-dihydroisoindol-2-yl)methanone and 2 mg of 4-(dimethylamino)pyridine (DMAP) in 5 ml of dimethylformamide, and the mixture is stirred at 80° C. for 16 h. 8 ml of ethyl acetate and 8 ml of water are added, the organic phase is separated off and evaporated to dryness in vacuo. The residue is dissolved in 1 ml of dimethyl sulfoxide and purified by chromatography (reversed phase HPLC).

Workup

customthe organic phase is separated off
customevaporated to dryness in vacuo
dissolutionThe residue is dissolved in 1 ml of dimethyl sulfoxide
custompurified by chromatography (reversed phase HPLC)

Sources & evidence

ORD record: ord-cd43aeb1495c4f62841b01b8ebc6e0ea
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791129B2

Reaction notes

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